2,4-dimethyl-1-(4-(trifluoromethyl)phenyl)pent-3-en-1-one | 1620135-30-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,4-dimethyl-1-(4-(trifluoromethyl)phenyl)pent-3-en-1-one
• 英文别名: 2,4-Dimethyl-1-[4-(trifluoromethyl)phenyl]pent-3-en-1-one
• CAS: 1620135-30-9
• 化学式: C₁₄H₁₅F₃O
• 分子量: 256.268
• InChiKey: YGCGWWGHWFRWEU-UHFFFAOYSA-N

物化性质

• 沸点：
  308.7±42.0 °C(predicted)
• 密度：
  1.110±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-溴-2-甲基-1-丙烯 、 4-三氟甲基苯丙酮 在 bis(1,5-cyclooctadiene)nickel (0) 、 lithium iodide 、 lithium hexamethyldisilazane 、 1,3-双(2,6-二异丙基苯基)氯化咪唑鎓 作用下， 以 四氢呋喃 为溶剂， 反应 2.08h， 以73 mg的产率得到2,4-dimethyl-1-(4-(trifluoromethyl)phenyl)pent-3-en-1-one
  参考文献：
  名称：

  Ni-Catalyzed Alkenylation of Ketone Enolates under Mild Conditions: Catalyst Identification and Optimization

  摘要：

  A procedure for Ni-catalyzed cross-coupling of ketone enolates with alkenyl halides has been developed. Intermolecular coupling of aromatic and aliphatic ketone lithium enolates with a variety of alkenyl halides is achieved in the presence of Ni(cod)(2) catalyst (5 mol %), an N-heterocyclic carbene (NHC) ligand, and LiI (10 mol %) at 6-22 degrees C for 0.5-12 h with yields of up to 90%. During the initial development of this reaction, a misleading result with respect to the actual active catalyst was obtained using commercially available Q:Phos ligand, which was found to contain a trace of Pd metal contaminant sufficient to catalyze the reaction. However, under the final conditions optimized for Ni(cod)(2) in the presence of an NHC ligand, Pd was incompetent as a catalyst.

  DOI：

  10.1021/jacs.5b02945

文献信息

• Palladium-Catalyzed Alkenylation of Ketone Enolates under Mild Conditions
  作者：Michael Grigalunas、Tobias Ankner、Per-Ola Norrby、Olaf Wiest、Paul Helquist

  DOI：10.1021/ol5017965

  日期：2014.8.1

  A protocol for a mild, catalytic, intermolecular alkenylation of ketone enolates has been developed using a Pd/Q-Phos catalyst. Efficient intermolecular coupling of a variety of ketones with alkenyl bromides was achieved with a slight excess of LiHMDS and temperatures down to 0 °C.